


Naïveté

by fanfic814



Category: Supernatural
Genre: BFFs, Bisexual Dean Winchester, Coming Out, Drunk Sex, F/M, First Time, Friends With Benefits, One Shot, Pegging, Pining, Sexual Experimentation, Strap-Ons
Language: English
Status: Completed
Published: 2017-05-22
Updated: 2017-05-22
Packaged: 2018-11-03 15:56:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,953
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10970562
Author URL: https://archiveofourown.org/users/fanfic814/pseuds/fanfic814
Summary: Dean's just trying to figure shit out.





	Naïveté

**Author's Note:**

> I wrote this a while back and found this in my Wordpress while cleaning it out today. I wasn't sure I liked it then, but now I think I do. I might re-work this one at some point, because I feel like it needs a little fleshing out.

"Hey Dean!" Charlie's cheerful voice rang through the earpiece of his cellphone.  "What do you guys say to pizza, beer, and finishing that Game of Thrones marathon tonight?"

Dean grinned into his phone receiver and he shook his head.  "Charlie, how did you know that's exactly what I needed tonight?  But Sammy's not here.  He took off with some girl from the bar earlier.  I'm sure he won't be home until tomorrow."

"Alright, so it's just you and me then.  Tell me what you want on your pizza, and I'll be there in an hour or so."

"Meat Lovers, extra cheese.  And I have plenty of beer, so don't worry about that."

"Got it.  See you soon!"

Dean smiled and wandered off to the kitchen to throw another six-pack in the fridge, his mouth watering already at the thought of a hot, greasy pizza. He'd been feeling a little sorry for himself since he was sitting home alone on a Saturday night, and a friends night in with Charlie and some greasy comfort food was a pretty decent consolation prize. Charlie was the absolute best.  It has been a long time since Dean could say he'd had a good friend, and somehow the red-haired, computer hacker geek-girl had weaseled her way into his heart.  Well, he had Cas, of course, but that was... _different_.  Mostly because whenever Cas was around lately, he was getting butterflies in his stomach like a stupid, lovesick teenager.  It was confusing as hell, and he was doing his damnedest to deny it in true Dean Winchester fashion.

He and Charlie had bonded over their mutual love of pop culture, and it was nice to have someone to geek out with over old reruns of Star Trek and Doctor Who.  He watched TV with Sam, of course, but Sammy was most definitely not a fanboy.  He never really understood Dean's obsession with movies, TV shows, or comic books.  Sam was a different kind of nerd; most of the time, he preferred to be on his computer or reading.

Dean hurried upstairs to his bedroom to do a quick clean up and to hide the stack of Busty Asian Beauties and the bottle of lube that had been prominently displayed on his nightstand.   _Alright, so his arm had been getting quite the workout lately._ He'd been in a bit of a drought the last few months, and these weird-ass feelings for Cas weren't helping the situation either. More than once this week, he'd been jerking off when Cas suddenly popped into his mind, leaving him feeling dirty and somewhat unsatisfied afterwards. He shook the thought from his mind as he shoved everything under his bed, straightened the blankets, then headed back down to the library to wait. He'd only been sitting a few minutes when Charlie's voice rang out through the bunker.

"Pizza's here!" she yelled gleefully, making her way down the stairs.  "And more importantly, so am I!" she winked, handing off the boxes to Dean.

"Hey kiddo," Dean greeted.  He swept her into a side hug with his free arm.  "What do I owe you for the pizza?"

"Pssh.  Nothing. My treat.  You wanna eat down here or upstairs?"

Dean shrugged and opened one of the boxes, taking a deep whiff.  " _Ohhh_ yeah _,"_ he nodded approvingly. "Let's take it upstairs.  I can't wait to see what that Joffrey dick is up to."

"Oh you're going to _love_ this part!" Charlie said excitedly.  "By 'love', I mean hate it!  I'll get the beer!" She hurried off to the kitchen for a stack of napkins and a six-pack of bottles before following Dean up the stairs.  
  
Charlie busied herself with the DVD player, queuing up the next episode as Dean doled out the slices.

"Veggie pizza?" Dean asked.  "He wrinkled his nose as he handed Charlie a slice on a napkin.  "Who ruins pizza with a shitload of veggies?   You and Sammy, that's who."

Charlie rolled her eyes as she took her spot on the bed.  "Have you ever even _eaten_ a vegetable?

"Lots of times," Dean scoffed.  "I _always_ get pickles on my burgers."

"Riiight.  What was I thinking?" Charlie shook her head.  "Hurry and get comfy so we can start already," she said, patting the spot next to her.

Dean sat down on the mattress, stretching his legs out in front of him as he took a huge bite of pizza.  "Alright, alright. Go!"  Charlie hit 'play' on the remote control and they fell into a companionable silence as the opening credits rolled.

Four hours, one and a half pizzas, and ten empty beer bottles later, they finally decided to call it a night.

"That Joffrey needs to die!" Dean exclaimed, before draining the last of his beer. " _Fuck_ , I want to kill him myself!"

"I told you!" Charlie said.  She stood to remove the DVD,  and abruptly stumbled, crashing back down on the bed.  "Holy shit, did I really drink four of those?" she giggled, pointing to the bottles on the bedside table. "Can I crash here tonight?"

Dean just laughed.  "Lightweight.  Of course.  I'm not letting you drive like that. You want something to wear? I mean, my shit will be huge on you, but I have some shorts with a drawstring that might work."

"Yeah, sure."

Dean strolled to his dresser and dug out a t-shirt and a pair of shorts and tossed them at her.  "Do I need to walk you to the damn bathroom?" he teased.

"Shut up," Charlie grinned.  "I'll be fine.  I'm not totally wasted, just a little tipsy. You might want to help me down the stairs though.  Just in case."

Dean shook his head.  "You're not sleeping on the couch. Take my bed.  I'll take the floor."

Charlie was stubborn, but compared to Dean, she knew she was a pushover, so instead of arguing, she just nodded and headed off to the bathroom. When she returned minutes later, dressed and ready for bed, Dean was already lying on a pile of sleeping bags and pillows on the floor.

"What, are you tired already?" she grinned as she climbed into the bed.  "Just like a man, always falling asleep when I'm looking forward to a little pillow talk," she teased.

Dean laughed.  "I'm wide awake.  Just relaxing.  And how would _you_ know what men do in bed?"

Charlie rolled her eyes and snorted.  "Please.  Not like I'm a gold star or something."

"A... what?"

"A gold star lesbian," Charlie laughed, "It's someone who has only ever been with women.  I've been with men."

Dean furrowed his brow in confusion.  "Really?   Huh.  So wouldn't that make you bisexual?"

"I guess it would if I sought out and enjoyed relationships with guys.  That makes me more like a lesbian who was in denial for a bit."

"Ahhh, I gotcha.  So... Did you always know?"

Charlie rolled onto her side and propped her head up with her arm.  "When I was younger, I knew I wasn't interested in guys," she mused.  "And when I first hooked up with a girl, I knew it felt right.  But I felt... I don't know... _Ashamed_ for a while. I didn't want to admit that I was different than most of my friends.  Totally stupid, I know, but it was scary at first. So I convinced myself that it was just sexual experimentation, you know?  Everyone does it in college, right?  Then I tried to force myself to like men." She laughed nervously.  "Not surprisingly, that was a disaster."

Dean grinned.  "Go figure.  Does everyone really do that in college, or is that just something people say?  I never went, myself."

"I think a lot of girls do.  Or at least, that's my experience.  I don't know if it's the same for guys or not.  Hey, we can ask Sam tomorrow," Charlie winked.

Dean wrinkled his nose.  "I don't need to know... Oh god, do you think he did?"

"I don't know!" Charlie burst out laughing.  "Maybe.  Are you telling me you've never thought about hooking up with a guy?  Ever?"

"Not really."

Charlie squinted suspiciously at him and she cocked her head.  "Never?  You've never even been curious?" She paused for a moment as she peered down at him.  "Ohmygod, you _have_!  You _are_!"

" _What_?" Dean sputtered.

"You're turning red!   Spill it, Winchester."

"Charlie, I'm not..."

"Is it that cute blonde that works at that burger place you always go to?" Charlie babbled excitedly. "That guy is so ripped!"

"No!  I'm not..."

"Oh, I know!  The bartender at Fifth Street Tavern!  He seems sweet."

"Seriously, Charlie.  Shut up. I'm not hooking up with random dudes."

Charlie huffed loudly and frowned. "Fine.  But there's something you're not telling me, and dammit, I'm going to figure it out."

"Fine," Dean laughed. "You go right ahead.  There's nothing."

"Wait.  Oh my god...."

"What?"

Charlie casually rolled onto her back, and grinned to herself.  "Nothing.  Nevermind.  I just remembered something I have to do tomorrow.  Speaking of tomorrow, what are you guys up to?"

"I told you earlier. Headed to Nashville to check out that possible angel kill."

"Oh right!" Charlie said.  "Just you and Sam?"

"And Cas."

Charlie nodded.  "That's right... Hey, do you think angels have issues with sexual orientation?"

"No," Dean shook his head. "They don't understand why humans care so much about gender."

"Huh. How do you know?"

"Cas told me."

"Ohhh.  So Cas can go either way then..."

"I-I guess," Dean fumbled.

Charlie hummed thoughtfully.  "I think he's _adorable_. God, he's so cute in a dorky kind of way."

"I guess," Dean shrugged, looking away as Charlie rambled on.

"What do you think an angel is like in bed?  I bet it's _amazing_.  I bet Cas loses that sweet puppy persona in a heartbeat and gets all possessive and rough and smite-y."

Dean licked his lips nervously. "I uh, I wouldn't know."

"Honestly," Charlie continued, "Do you think he has a body under that tax accountant getup?"

" _Oh_ yeah." The words slipped out before Dean could bite them back, and he immediately felt himself turning red.

"Holy shit!" Charlie squeaked as she bolted up to stare at him.  "Dean!  Cas?  Ohmygod!  When did this happen?  How? Does he know? Are you..."

" _Shut up_ ," Dean warned.  "I don't wanna talk about it."

Charlie huffed excitedly.  "Oh come _on_!" You can't expect me to not say anything!  This is huge!  Your first boy crush!  I'm so excited for you!  Wait... _Is_ it your first?"

"Look, I don't know what the hell it is," Dean snapped, embarrassed that he was so damn obvious. "It's confusing, alright? I don't know what the fuck is wrong with me."

Charlie frowned and sat up, then lowered herself down onto the floor next to him. " _Why_ ," she started as she lay down, resting her head on his shoulder, "do you think there's something wrong with you?"

Dean sighed.  It was hard to be frustrated at Charlie.  Instead, he slipped an arm around her and let her snuggle up closer.  "There's nothing _wrong_ with it. I just mean, this has never happened to me before, and it's confusing. I guess I've had a random thought here and there, but nothing like this.  A fleeting moment, nothing I've seriously _thought_ about!   I close my eyes and he's _there_.  I jerk off and he pops into my head. What the fuck?  Not like I want to have sex with _Cas_!"

Charlie tried to stifle her huge grin.  "Why not?"

"It's... I don't know!  Honestly, the sex thing is what's freaking me out!  This has been 'exit only' my entire life, and it's not looking to change anytime soon."

This time, Charlie couldn't hold back a torrent of giggles.  "Big, bad Dean Winchester is scared of a little butt sex?  Come on!  What's so scary about it?  You've never had anything up your ass before?  Ever?"

" _No!_ " Dean vehemently shook his head.

"You know, you don't have to be gay to enjoy a little anal play," Charlie said matter-of-factly. "Why are straight dudes so paranoid about exploring their own bodies?"

"Do you know what comes out of there?" Dean exclaimed. "And Jesus, could you not say that so casually?  Here I thought were so sweet and naïve!"

Charlie snorted.  "Sweet, maybe.  Naïve, no. Why does everyone always think I'm naïve?  You have no idea how kinky I am!" She swatted him on the arm for emphasis.

"Oh please!" Dean laughed.  "You're all sunshine and rainbows.  No way you have a kinky side."

Charlie sat up, giving him an incredulous look.  "Oh my _god_.  Stay here a minute," she said, as she stood and walked out of the bedroom.

Dean lay there dumbfounded for a few minutes until Charlie finally returned, dropping a Harry Potter backpack on his stomach.    
  
"What's this?"

Charlie just shrugged demurely and motioned for him to open it.

Dean shook his head and struggled to sit up while she plopped back down on the bed.  Slowly, he unzipped the bag.   "What the fuck is that?" he yelped, shoving the backpack away.

"Meet Evil Charlie.  This is my booty call bag," she  winked. "You know that girl I've been seeing?"

Dean nodded.  "You _torture_ her?"

"Torture?" Charlie chortled. "Who's the naïve one now?  It's just a little light bondage!  Okay and some other stuff..." she grinned. "Point is, I'm not naïve, jackass."

"Apparently!  Was that a pink dildo strap-on?" he cringed.  "And what was that blue thing?  Tell me that wasn't a butt plug!"

Charlie just rolled her eyes.  "Shut up or I'll use them on you." She tossed the bag on the floor and settled back into bed, pulling the blankets up to her chin.  "You look traumatized," she giggled.

"I am!  You can't just spring something like that on me!  And the rest... Holy shit, are you a dominatrix or what?"

"Sometimes," she laughed softly.

"Holy shit."

"You should go find yourself a professional Domme," Charlie teased.  "They'd work that irrational panic right out of you."

"Oh my god, let's stop talking about it."

Charlie grinned and continued.  "I'm serious, Dean!  You need to get over this!  Because you and Cas... it _needs_ to happen! He's totally into you!   He follows you around like a puppy!  And the way he looks at you sometimes... "

"What about it?"

"He just..." she sighed heavily.  "He _adores_ you. I mean, it's been obvious since I met him, but I didn't know you were interes...  _curious_ ," she corrected herself as Dean scowled. "Come on.  Admit you're a little curious, at least."

"Charlie..."

Charlie paused.  "Aw, shit. Get up here," she suddenly demanded, reaching over to tug at his arm.

"I'm fine, I..."

"Get up here," she repeated.

Dean sighed and kicked his blankets off, then grudgingly climbed into the bed.

"Don't cry," she begged, wiping at the single tear threatening to spill down his cheek.  "I'm sorry.  I didn't mean to push you."

"No," Dean muttered. "It's not that, I..." He rubbed frantically at his eyes, chasing the last bits of wetness away.  "This just... It fucking sucks!" he yelled. "Seriously, what the _fuck_ is wrong with me?  You said you've known pretty much forever, right?  I've known forever that I'm into women.  I've never been attracted to a guy!  What the hell is happening to me?" he finished weakly.

"Aw, Dean," Charlie said, slipping an arm around his waist.  "I know it's hard.  I know it sucks at first, but the sooner you start admitting it to yourself, the easier it will get.  It's really not a big deal in the scheme of things." She curled up tightly as Dean anxiously stroked her arm.  "I'm not any different since I came out. Same old Charlie.  Just happier, because I can fuck who I want without all the secrets and guilt."

Dean nodded uncertainty.

"And," she continued as she began gently stroking his hair, "I want you to be happy too.  I love you, and I love Cas.  I think you'd be so good together. But I also know you can't rush yourself.  So I'll shut up now, but please know you can always talk to me if it gets too scary and confusing."

Dean exhaled a huge breath as a few stray tears found their way down his cheeks, and he wiped them away in annoyance. "Thanks," he said sincerely.  "I'm just a little fucked up right now."

Charlie nodded.  "I know.  It's okay to feel fucked up.  But please know that you're not, okay?"

Dean swallowed hard.  He took a deep breath and continued. "Alright. I can admit it.  I have some weird kind of crush on him... Wait, is that something adults even have?"

"Yes," Charlie smiled.

"But how the hell do I _do_ anything about it?  How do I talk to him?  How do I bring it up? And fuck, the sex is eventually going to come up!  Why pursue a relationship when you're scared of being...   _intimate_ with the person?"

"It really scares you that much?"

"Yes.  No.   _Fuck_ , I don't know..." Dean sighed and hugged her a little tighter, burying his face in Charlie's hair.

"Oh, Dean," Charlie sighed.  "You'll figure it out.  I promise."  She paused.  "The sex-thing doesn't turn you on even a little?"

Dean groaned.  "Oh it _does_. For a few minutes.  Then it freaks me the fuck out."

Charlie laughed.  "You know... I could, uh," she cleared her throat.  "If you want to try it..."

"What?"

"You know.  I have all my gear here.  If you want to try it, I could uh... you know."

Dean pulled away, nearly sitting up as he jerked.  "Y-you're kidding, right?"

"Yeah!  Uh.  Yeah.  Of course," Charlie laughed nervously.  "I uh, I didn't..."

"Holy fuck, you're not kidding."  Dean's statement hung heavy in the air between them as neither one suddenly knew what to say.

Charlie bolted up in panic.  "Oh god.  I mean... I didn't... Uh.  Oh god. Please just say something?" she managed meekly.

"I-I... uh..."  Dean stuttered.  "W-what did you have in mind?"

Charlie gasped in relief, still nervous, but the fact that Dean didn't go flying out of the room was a good sign.  "I just mean... we could handle something like that, right?  Like uh... a once-in-a-lifetime friends with benefits thing?  And I don't need anything!  It's just so you can umm.  Get over your fear!  It's not like either of us are going to get too attached.  You know I love you, but not like that.  I mean, I have zero desire for your naughty bits.  No offense."

Dean laughed. "Yeah.  I love you too.  But not like that."

"So it'd just be like a friend helping out a friend, right?"

"Yeah. I guess so...  Don't you think it'll get weird?  How drunk _are_ you right now?"

Charlie sputtered in laughter. "Not _that_ drunk.  Really.  You?"

"Just a little buzzed..." Dean chewed his bottom lip apprehensively. "Charlie, we can't..."

"Lie back down," she interrupted.  "Either way, let's take it down a notch, okay?  You're a nervous wreck just _talking_ about this."  She gave him a gentle shove and he acquiesced, pulling her down beside him.  "Take a deep breath for me," she said softly as she slung an arm around his waist again.  "Good.  Honestly, Dean, we can just pretend none of this ever happened if you'd like."

Dean closed his eyes and rubbed at his face tiredly.  "No, I... Fuck, I don't know what to say here."

Charlie nodded knowingly.  "Take off your pants."

"What?!"

"Come on!  Close your eyes and lie on your stomach if it makes you feel better.  Just... just trust me."

Dean's heart was pounding in his chest, and his thoughts were in a million different places, but Charlie was talking to and stroking him like a scared cat.   _He couldn't do this... could he?_ Curiosity was getting the best of him, and for some reason, just talking about it was making him horny as hell. But this was _Charlie_.  His best friend!  They couldn't... He suddenly froze as he felt Charlie sit up and grip the waistband of his shorts.

"No pressure," she murmured.  "I think you want to, but are too embarrassed to say yes to me.  So... if you do...  Just close your eyes."

Dean let his eyelids slip heavily closed.

"Good," Charlie whispered, as she tugged his shorts and underwear off.  "Now just sit up for me and let me get the shirt off...   Good."

Dean's entire body was trembling now as he lay there bare in front of Charlie, and he clamped his eyes shut a bit tighter.

"On your stomach," she whispered.  "I'm just going to give you a little massage, okay?  No big deal.  We'll get you all nice and relaxed."  She dug through her bag for a moment as Dean gratefully turned away from her.

He flinched as he heard a bottle click open and closed, but when two oil-soaked hands began gliding up and down his back a minute later, Dean couldn't help but swoon.   _Ohhhh.  An actual massage. Okay, he wasn't expecting this._ Charlie was surprisingly good with her hands, and little by little, he gave himself over to her therapeutic touch.  He moaned as she worked into some particularly large knots in his back, suddenly wondering why he'd never gone for a real massage.  _Yeah, he could really get used to this._

"Where did you learn to do this?" he murmured blissfully.

Charlie just smirked.  "Oh, Dean, I have skills you've never even dreamed of."

Dean let himself zone out as she worked the kinks and tightness from his overly stressed muscles.  He was feeling so warm and comfortable, that for a few moments, he even forgot he was sprawled out naked on his bed in front of _Charlie_.  Nearly an hour had passed when he suddenly realized he was nodding in and out of consciousness, every trace of anxiety was now gone and replaced with a warm, blissful feeling.  He hummed happily as Charlie's fingers raked up and down his back, thumbs kneading into his shoulders and neck, then trailing lower, all the way down to the tight muscles of his lower back.

"Whoa," he jumped momentary as her hands dipped further and began working his glutes, but quickly settled back down as Charlie shushed him.  "Oh that feels weird," he murmured, "...but nice."

"I know," Charlie whispered.  She moved down further and began firmly working up and down the back of his thighs. "How are you feeling?"

"Hmm?  Good," Dean sighed. " _So_ good."

Charlie nodded and took a deep breath, then dug for another tube in her bag.  "Alright."  Slowly, she slid a hand back up and kneaded at the muscles in his ass again before cautiously slipping a well-lubed finger between his cheeks.

Dean's breath suddenly turned ragged as she stroked at him, but his legs automatically spread to allow her more room.

"That's it.  You're doing so good," Charlie said as she softly caressed him.  "Just relax..." She let the tip of her finger slip inside of him and Dean jumped.

"Oh god," he gasped. "Ch-Charlie..."

"You just think about Cas, sweetie," Charlie interrupted, not even giving him a chance to hesitate before slipping it in all the way.

Dean yelped loudly and his body buckled for a second as he instinctively tried to pull away.

"Stay," Charlie commanded, amused at how quickly she could bring a six-foot-two-inch man to his knees.

Dean buried his face in his pillow and cried out again, hands digging into the blankets beneath him. "F-fuck! I can't... I..."

"Shhh.  Come up on your knees."

Despite his discomfort, Dean obeyed, whimpering in short, sharp groans.

"Oh Dean, Cas is going to be bigger than this.  Stop clenching and try to relax.  You can handle this." Charlie heard him take a few long, deep breaths, and slowly, he began loosening up.  "That's it..." She gave him a few minutes to adjust before slipping another finger inside of him.

"Fuuuuck!" Dean roared.  "This...s-sucks."

Charlie discretely rolled her eyes behind his back.  For someone who stoically battled literal monsters every day, he certainly could be dramatic.  "It'll get better.  Breathe and relax."  She continued working her fingers in and out of him, faster now as he whimpered uncontrollably.

He groaned again as she began targeting his prostate, wondering what the hell she was doing, when suddenly, he realized it wasn't so bad. In fact, it felt pretty damn good. He cried out in awe as his body jerked forward.

"Holy f-fuck.  What was that?".

" _That_ is the reason this is all worth it," Charlie smiled. She pulled away for a moment to grab another item from her bag, and the next thing Dean knew, something cool and hard was pressing against him.  His entire body tensed up and Charlie paused. 

"Oh shit.  I don't know about this," Dean suddenly panted. "I don't think I can..."

"You're gonna be fine," Charlie murmured.  "I'm going to take it nice and slow for you, okay?  You're good and stretched, I've got lots of lube...  I just need you to relax.  Push into it if you need to."

"P-push?"

Charlie giggled.  "Like you're taking a shit, Dean. You can do this.  Ready?" She fumbled with the straps to her harness and Velcroed them securely.

"No," he whimpered. "I... can't..."

"You're not even curious as to what it feels like?" Charlie interrupted.  "Cas, naked on top of you.  Kissing you.  Holding you.   _Inside_ you?"

Dean bit his lip and moaned loudly.

"Filling you up.  Cumming inside you..." Charlie continued, smirking to herself as Dean nodded frantically.

"Yes.  Please," he gasped weakly.

"Good.  Ready?  Push for me." Gently she let the tip of the dildo enter him as he growled in discomfort.

"Fuck!  Oh fuck! Fuck! Fuck! Oh god!" He buried his face in the pillow to hide the pathetic noises coming from his mouth.

Charlie just continued pushing until her hips pressed against him. "That's it," she whispered.  "Good job. You just took it all. Let's just rest here a minute until you get used to it."

Dean was trembling and sweating beneath her, and his breaths were coming erratically as if he were sobbing, so Charlie wrapped her arms around him and rested her head on his shoulder.

"Shhhhh.  Shhh.  What are you thinking right now?" she whispered.

"I'm thinking this fucking hurts," Dean growled.

"Hmm, just rest for a few minutes, sweetie," Charlie hummed.  "Once you relax a little, it'll just be a bit uncomfortable."

Dean huffed in annoyance.  "Great," he mumbled sarcastically.

" _And_ , once you relax, I can work on hitting that spot again.  The one that made your toes curl a few minutes ago?"

Dean took a deep breath.   _Okay.  That **might** make it all worth it...  _ He'd never felt anything quite that intense before, and he was slightly curious to try it again.

"There you go.  Just close your eyes and think about Cas..."

Dean closed his eyes and nodded, and Charlie smiled as she felt his body starting to relax.  Slowly, she pistoned her hips, out then in again as ridiculously obscene noises fell from Dean's mouth. 

"Holy shit," Dean murmured. "Charlie..."

" _Cas_ ," Charlie reprimanded.

Dean grunted and pressed his forehead into the pillow, trying to brace himself as Charlie decided to stop taking it easy on him.

"F-fuck! Oh my god..." 

"You can touch yourself if you want," Charlie suggested quietly.

Dean nodded. He'd been so wrapped up in trying to process this foreign feeling that the thought hadn't even occurred to him. Shoving a hand between his legs, he began stroking hard and fast until his legs were trembling and his hips stuttering. His eyes squeezed shut and he arched his back, yelling louder than he'd ever admit to.

"Fuck! Fuck! Oh god, yeah! Cas. Fuck! Caaas!"  He collapsed forward on the bed, trembling and panting as Charlie kissed his shoulder.  Without a word, she slowly pulled out and stood to unhook the strap-on. She retreated to the bathroom, and returned a few minutes later with a warm washcloth. 

"Dean?" she asked softly. "You okay?"

Dean glanced over his shoulder and nodded weakly. "I think so." 

Charlie handed him the washcloth and he turned onto his side, discreetly trying to clean himself up. 

"Can you hand me my shorts?" he managed, suddenly embarrassed at how vulnerable he felt. 

Charlie picked up his boxer shorts and tossed them in his direction, and he hurriedly tugged them on.  "Uhhhh...  I um. I don't know what to say right now," he admitted sheepishly. 

"Hey. We said this wouldn't get weird, so don't _make_ it weird.  Let me cuddle you."  
  
Dean laughed.  "You don't have to do that.  I'm sweaty and gross."  
  
"I know, but I want to anyway," she said, curling up next to him.  "You just got your ass pounded, you're allowed to be a little emotional.  C'mon, get closer." Dean pulled her in close to his chest and Charlie wrapped an arm around his waist.   
  
"So... real talk now," she insisted.  "You're really okay?"  
  
"I'm fine," Dean said tiredly.  "Exhausted. A little embarrassed.  Otherwise fine."    
  
"Good.  How did it feel?"  
  
Dean chuckled and coyly wiped a hand over his face. "Uh.  Not great at first, but way better than I expected after that.  Okay, it was kind of _incredible_."  
  
"Awesome.  Less scared now?"  
  
"Mmmhmm," Dean yawned.  
  
"Oh, right.  I forgot guys fall asleep after sex," Charlie teased.  "Get some rest, Dean."  
  
"Thank you, Charlie," Dean hummed, blissfully closing his eyes as he pulled the blankets up around them.  "I owe you one."  
  
Charlie burst out laughing.  "Uh.  How about you just promise to never call me naïve again?"  
  
"Deal."


End file.
